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Who was the hardest gym leader for you to beat?

MegaBlastoise15

MegaBlastoise15

I can name several off the top of my head:

Misty(R/B/Y)- Her Starmie was a pain back in the day.
Sabrina(R/B/Y)- Psychic. Need I say more? Plus, her Gym was tedious to navigate.
Whitney(G/S/C)- Ugh... I remember getting that Machop from the NPC in the dept. store just to beat her.
Chuck(G/S/C)- DynamicPunch always OK'd me back in the day.
Clair(HG/SS)- Not so much in G/S/C, but still was a pain in the ass.
Brawly(R/S/E)- Very bad memories from this guy(which is why I despise Fighting types).
Norman(R/S/E)- His Slaking always killed me.
 
The iFlare

The iFlare

My hardest gym battle is a three-way tie between Brock in Yellow, Koga in Fire Red, and Whitney in Heart Gold.
Brock was my first ever gym battle, EVER. I was only six years old at the time, and all I had was Pikachu and Pidgey... Both weak to his Geodudes. It took overleveling my pokemon into their mid twenties to barely beat him.
Six years later, Koga destroyed my team repeatedly because I was illy prepared.
Whitney... She's just Whitney.
 
Kawaii Unicorn

Kawaii Unicorn

In X I hadn't trained much because in Santalune forest I'm like "Oh cool, I can use the run button!" And I wasn't prepared for Viola, I fainted alot, and I wanted to zap into the game and smack her.
 
Skadoodle

Skadoodle

Did anyone here ever rage when you battled cerena? Because I did! Her Hawlucha got THREE attacks IN A ROW! I was doing reall good! It still makes me mad!
 
Kawaii Unicorn

Kawaii Unicorn

By the time I did Korrina my Sylveon was overpowered so I'm like "Take that ya Hawlucha!" and Korrina is like "NOOOO!!!!!!!!!" and I'm like "Hue, hue, now give me my mega bracelet thingy!"
 
theshadedmistress

theshadedmistress

I've had trouble with some Gym Leaders in my first few playthroughs of the games. Here are the few I remember.

Whitney - You should probably know why by now.
Morty - His gym in the G/S/C confused the hell out of me, and his Gengar was always able to put me to sleep. I prepare with twenty Awakenings nowadays.
Fantina - All of her pokemon were tough. The only good pokemon I really had was Eevee, and even with that I barely made it.
Lenora - That damn Watchog was a killer.
I only actually lost to Whitney, however. 8)
 
Lost Wolf

Lost Wolf

Oh god. Not this. Please. Everybody is going to laugh at me but...Cilan from Black And White. He was freaking annoying and it took me many tries just to beat that-that. Broccoli on a stick. UGHHHHH
 
Javelin

Javelin

Whitney like pretty much everyone else, at least back in the original Gold and Silver. I've beaten her twice total now on HeartGold without any real trouble, though. I don't know if it was actually made easier or if I just smartened up since I was a kid but an appropriately leveled female Geodude withstands and handles that Miltank without fuss.
 
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